A Powerful Enantioselective Organocatalytic Approa.. (POWORMAD)
A Powerful Enantioselective Organocatalytic Approach to the Total Synthesis of
Madangamine Alkaloids
(POWORMAD)
Start date: Mar 1, 2012,
End date: Feb 28, 2014
PROJECT
FINISHED
"The projet concerns the development of a powerful first total synthesis of the Madagamine alkaloids. The route starts with an organocatalytic enantioselective and diastereoselective Michael addition of cyanoacetate pronucleophiles to a nitrocyclohexene derivative, as a key step to the formation of the ABC core. When the product of this reaction is subjected to a nitro-Mannich, Mannich reaction cascade this should allow us to construct the core of the madangamine alkaloids rapidly, selectively and on scale. The overall synthetic strategy has two parts. The first concerns a fast and enantioselective assembly of diazatricyclic core common to all madangamines (ABC rings). The second concerns easy and efficient ways to build the two macrocyclic rings (D and E rings), which play a fundamental role in their biological activity. The project combines, catalysis, total synthesis, structure elucidation and evaluation of biological properties."
Get Access to the 1st Network for European Cooperation
Log In